Breaking Up is Hard

I've never paid much attention to clichés, such as "breaking up is hard to do." Maybe I should have.

When I was a sophomore in a local university I was dating a guy, his name was Evan, who was handsome and smart but had two big drawbacks. The first, and worst for a "wild child" like me, was that he was a bore when it came to sex. No imagination, no playfulness, no experimentation, nothing the least bit kinky.

The second was that he seemed to prefer the company of his three male "best buddies" to mine. Not that he or they were gay, or anything, but they liked to do guy things together. It wasn't that I didn't like his friends. They were cute and polite; I guess I was just jealous of the time he spent with them. I asked him why they didn't have steady girlfriends themselves and he always gave me the same answer: "They haven't found anyone that is as awesome as you are, Jill, and they're not settling for anything less." I didn't really believe it but of course I liked hearing it.

Anyway, I had told Evan a number of times that he needed to get more "into" it during sex and gave him not-too-subtle hints about things that he could do to me, and even directed him to some racy websites, but without much success. I was bored.

We went to a football game one Saturday and then back to his apartment. As we were having a drink I was contemplating exactly how I was going to break it off with him that night without having to tell him that it was because he was way too lackluster sexually. As my mind was mulling that over trying to find the right words out of the corner of my eye I noticed that he seemed to be fiddling around with something on the other side of the coffee table.

"What are you doing, Evan?" I naively asked.

"Well, Jill, there is something I need to reattach to this side of the coffee table and I'm not having much luck. Can you help?"

"I guess; what should I do?"

"I know that this is weird but I think it will put you in the best position to help; could you kneel d

own on that side of the table and reach over and I'll show you what I want you to hold."

"Will you get me another drink as soon as I complete this weird task?"

"Whatever you want Jill."

So I got on my knees, reached over the table, felt something going onto each wrist, and then heard two "clicks." I tried to pull my hands back but with no luck. From what I could tell each wrist was cuffed with fur-lined handcuffs to a leg of the table. "What the hell is this?" I asked, surprised and perturbed.

"I thought we would spend a different type of 'quality time' together tonight. I hate to be a boring guy; maybe I learned some things from the websites you told me about."

Suddenly my demeanor changed. Let me see how this plays out, I said to myself. "Oh yeah?" was all that I said out loud with a half-sneer, half-smile on my face.

"Just so that I'm not unduly influenced by you, let's start with this," Evan said, pulling a ball gag from a cloth grocery bag that suddenly appeared from under the table. Before I could do anything more than give out a weak scream he had it in my mouth, and that was the last I could talk for about an hour.

As I was cuffed, kneeling, speechless, and helpless, Evan walked around back of me. Despite my attempts to keep my legs together and wiggle around to prevent it he easily removed my panties from under my skirt, undid my belt, and removed my skirt. Cackling the entire time he then pulled my top over my head until it reached my cuffed wrists, then undid my strapless bra and tossed it to the side. My muffled squeals seemed to encourage him rather than deter him.

After getting me naked he pulled some panty hose out of a package, took out a scissors, and cut them in half. He used each half to tie my thighs to the other two legs of the coffee table, with my pussy exposed.

Smiling, the asshole then removed a small bullet vibrator from his "grocery" bag. He held the vibrator up, testing all of its speeds, and making comments like, "I wonder what it would feel like at this level, hmm." As I watched wide eyed he turned it on max speed, crawled behind me, and tucked it neatly into my pussy.

I tried hard to push the vibrator out, contracting my pc and every other muscle I could try and control, but before I could eject it he took a can of whipped cream and inserted the tip inside my vagina and squeezed until I was stuffed. I heard him laughing as I watched him use duct tape to seal me shut. Then he ran a long piece of the tape down my trimmed landing strip, patted it down nice and softly, then ripped it off in a quick motion. I thrust my hips upward but I was stopped by my bonds.

I couldn't be sure whether I loved or hated what he was doing. He certainly had gotten my attention, especially the attention of my pussy.

As I lay across the table with my eyes half-glazed Evan removed a medium sized butt plug from his little bag of tricks. He rammed it in and out of my ass a few times as I felt my face get flushed, and I'm sure it got scarlet red from my attempts at calling for help, muffled by the gag.

Evan looked coyly at me as tear droplets start to form in the corner of my eyes. "This is what you wanted, isn't it?" I shook my head "no," then "yes," then "no" again, and then "yes again as I looked longingly at a bottle of lube which had fallen out of his bag.

"Oops," he said. Holding the lube tube up he said "You don't need this, do you? Certainly you don't need it for this little string of beads, do you?"

How much shit does he have in that goddam bag? I said to myself as Evan dangled a link of anal beads in one hand, smilingly kissed each of them, but did relent and applied the lube to the first two beads and then went behind me again. He guided the link of anal beads into my anus until my butt-cheeks clapped around the ring. I whimpered from the exploding mixture of anal pain and pleasure.

Then Evan stood up, walked in front of me, gave me a kiss on the forehead and said "Now that you're comfortable I need to run an errand. I'll be back for more activities soon."

With that he got up and actually went out the door.

There I was, both holes filled, and that goddamn little bullet vibe relentlessly energizing my poor little cunt. Will my little kitty ever be the same? I asked myself as I squirmed in my restraints for what had to be a good hour.

When Evan finally came back my whole body was shaking uncontrollably from both pain and pleasure. "How you doing, Hon?" Evan rhetorically asked as I looked at him with glassy eyes.

Evan then took my gag off as I let out a huge sigh of relief, followed immediately by a sob of mixed emotions. Evan then slowly peeled away the weakened duct tape holding the vibe in place. I could feel the heat emanating from my crotch as if it was on fire. The adhesive had slowly become weaker as my fluids were finding every small crevice to escape. When the tape slowly revealed my slit, the gushing of the contained fluids pushed the last clinging corner off. I could feel, and Evan remarked about, the mixture of the whipped cream, my own bodily nectars, and sweat that was squirting out of my pussy as I let out a loud and long "unnnnngggghhh."

After doing some controlled breathing I regained my composure and breathed a sigh of relief. That is I was relieved until I realized that Evan was still standing over me with crossed arms and a deadly smile forming in the corner of his mouth. He grabbed the ring of the anal beads still tucked in my ass and gave them a small tug, forcing the beads to come out, one at a time in a slow though pleasurable pace. I groaned and squirted instantaneously in a near vertical stream. With each successive bead, the jet got more and more intense as I arched my back more and more until my Skeen's gland had completely emptied.

Finally, I don't know how long it was, all remnants of pain were gone and only an ethereal pleasure remained. I felt Evan untie the pantyhose restraining my thighs, and unlock the fur line handcuffs. He then laid me on a comforter on the living area floor and sucked and massaged my breasts and thighs. That really felt good. Then he started licking my clitoris. I grabbed his hair and moaned until in response to his tongue on my clit and his fingers on my nipples I orgasmed.

I was virtually comatose; "virtually," not completely, because I saw Evan undress. His cock sprung out of his boxers like a jack-in-the-box. He had a hard time pulling his boxers over his cock but finally did. I don't know if it was just my state of mind but it seemed like his cock was bigger and harder than I had ever seen it, like a piece of steel.

As Evan lay next to me and planted kisses on my face he asked, "Well Kinky-Jill, how do you like the evening so far."

"Both the best and worst of my life," I replied, maybe slightly exaggerating but basically telling the truth.

"It's gonna get better and/or worse," Evan replied with a truly devilish grin. Then he lay flat, rolled me on top of him, and slowly wiggled his cock up my channel.

Wow that felt good as he slowly lifted my hips up and down and twisted his flagpole in my pussy. I was too lethargic to provide any body movement myself but my nerve endings and mind were getting sharper by the minute and I was really feeling good.

As I was enjoying my interior "massage" I thought I heard the apartment door open and then close twenty or thirty seconds later, but I wasn't sure because all I was concentrating on was my own pleasure.

My head snapped backward when I felt a gel coming in contact with my asshole; it couldn't be Evan because I felt all of his fingers on my hips and ass. As I said "What the fuck?" Evan pulled me tight against his body and said "enjoy it."

I would have protested but whoever was lubing my asshole was being gentle and when he inserted into my asshole and then withdrew, one finger, then two, I was enjoying it especially since my pussy was filled up with Evan's hard cock.

Suddenly the finger action stopped and after a pause I felt the lubricated helmet of a dick slowly being worked into my asshole. Evan stopped moving until the dick was completely buried. I thought for sure that I was about to split, but to my surprise it felt great when the dick started pumping in and out of my asshole.

Both Evan and I were just lying there and groaning when the dick pumping in my second hole started squirting a monster load up my ass as its owner was grunting like a troll. Shit, I almost passed out. After thoroughly washing my intestine the dick pulled out, and Evan started pumping again while he continued to hold me tight. I figured out why when I felt another, larger, lubricated helmet working its way into my asshole.

The second dick was not only larger than the first one but it was moving faster in my asshole. Since my ass was now very well lubricated with the jism from the first cock there was little friction. With two dicks in me I felt very tight, but also felt so good. Then suddenly the second dick-owner was grunting like a pig and another enormous gob of cum was being jettisoned into my asshole.

When the second dick pulled out of my asshole I was wiped out. Evan sure wasn't because as soon as the second dick was removed he started pumping like an oil derrick. That is until I heard another male voice say, "Slow down for a second, man." I could tell that Evan didn't like it, but he slowed almost to a stop.

As I lay there sweating I knew what was coming next. Evan had three "best buddies" and I had gotten only two dicks rammed up my ass so far; I knew the third couldn't be far behind. What I didn't know is that the third dick would be even bigger than the second one.

Despite the well lubricated nature of my asshole the third dick was so big it really had trouble burying itself. It eventually bottomed out and when it did the two cocks filling me up started in-sync movements. When Evan's cock was being pushed up my pussy the big dick in my asshole was being pulled out, and vice-versa. Both guys increased their pace until I thought I couldn't take it anymore. Just then both guys exploded into me at the same time. I never had my nerve endings energized more in my life. I enjoyed it immensely -- that is until I blacked out.

I woke up the next morning with my pussy and asshole as sore as they had ever been, and with Evan kissing me and pinching my ass. "How about some breakfast my little fuck toy?"